Iridium-catalyzed asymmetric transfer hydrogenation of quinolines with Hantzsch esters

The iridium-catalyzed enantioselective transfer hydrogenation of quinolines with Hantzsch esters was developed with up to 88% ee using [Ir(COD)Cl]2/(S)-SegPhos/I2 as a catalyst.

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(S)-2-Methyl-1,2,3,4-tetrahydroquinolineC10H13N[α]D = −73.2 (c 0.56, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-2-Ethyl-1,2,3,4-tetrahydroquinolineC11H15N[α]D = −70.9 (c 0.66, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-2-Butyl-1,2,3,4-tetrahydroquinolineC13H19N[α]D = −72.2 (c 0.92, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-2-Pentyl-1,2,3,4-tetrahydroquinolineC14H21N[α]D = −41.3 (c 0.92, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-6-Fluoro-2-methyl-1,2,3,4-tetrahydroquinolineC10H12FN[α]D = −54.4 (c 0.70, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-2,6-Dimethyl-1,2,3,4-tetrahydroquinolineC11H15N[α]D = −65.3 (c 0.62, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-6-Methoxy-2-methyl-1,2,3,4-tetrahydroquinolineC11H15NO[α]D = −63.5 (c 0.36, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-2-Phenethyl-1,2,3,4-tetrahydroquinolineC17H19N[α]D = −67.2 (c 1.14, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-2-(3′,4′-Methylenedioxyphenethyl)-1,2,3,4-tetrahydroquinolineC18H19NO2[α]D = −50.0 (c 1.19, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(S)-2-(3′,4′-Dimethoxyphenethyl)-1,2,3,4-tetrahydroquinolineC19H23NO2[α]D = −43.8 (c 1.34, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (S)

(R)-1,1-Diphenyl-2-(1,2,3,4-tetrahydroquinolin-2-yl)-ethanolC23H23NO[α]D = −82.6 (c 1.18, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)

(R)-2-Phenyl-1,2,3,4-tetrahydroquinolineC15H15N[α]D = +7.6 (c 0.88, CHCl3)Source of chirality: asymmetric hydrogenationAbsolute configuration: (R)